Preparation

Preheat oven to 425 F.

Cut the tip off of the head of garlic, exposing the tops of the cloves inside. Place it on a small sheet of aluminum foil, drizzle with 1 tablespoon of olive oil. Fold foil around garlic to form a tight package.

Cut the butternut squash in half. Scoop out the seeds. Place the halves on a baking sheet. Place garlic package on the baking sheet as well.

Roast at 425 F for 25 minutes then remove the garlic and allow it to cool. Continue to roast the butternut squash for an additional 20 to 30 minutes (45 to 55 minutes total) or until flesh is soft and easy to scoop out.

When done, remove the pan from the oven and scoop out the squash flesh (should be about 5 cups) and put the flesh into the bowl of your food processor. Puree it using the food processor until smooth. Set it aside.

In a large pot or Dutch oven, add the shallots and 3 tablespoons of olive oil over medium heat. Caramelize the shallots over medium heat, stirring occasional, for about 10 minutes or until a dark golden brown. Don’t cook over high heat or the shallots will burn.

After 10 minutes add the chicken broth, water, butternut puree, salt, pepper and cayenne. Squeeze the soft garlic head until the cloves push out of the skin (should be soft and mushy) and add cloves to the soup. Stir it well to break up the garlic. Bring soup to a boil, then reduce heat and to maintain a simmer until slightly thickened, about 10 minutes.